salicyl alcohol acetyl salicylic acid. saturated carbon chains c c-c c-c-c

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Salicyl alcohol acetyl salicylic acid

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Page 1: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Salicyl alcohol acetyl salicylic acid

Page 2: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Saturated carbon chains

C

C-C

C-C-C

Page 3: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

CATENATION: OLD (CHEM 1):

Valence

Page 4: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

IONIC COVALENT

Page 5: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C
Page 6: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C
Page 7: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C
Page 8: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

CH3

Page 9: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

morphine = Acylated morphine=Heroine

CH3

Page 10: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Name the following alkanes:

C2H6

C4H10

Page 11: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Review the work from your notebook from the past week.

Spend 5 minutes writing/reflecting about what you learned. Include specific examples.

Page 12: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Saturated carbon chains

ROOT NAME EXAMPLE

C

C-C

C-C-C

C-C-C-C

5 C

6 C

7-C

8 C

9 C

10 C

Page 13: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

-OH is the alcohol functional group

Generic alcohol can be written R-OH

R, represents a carbon chain of some sort

Page 14: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

There is an interesting legend surrounding the discovery of soap making. This legend accords the discovery of soap to the Romans so it must be a Roman legend to confront the Celtic claim to soap making. Probably both of these inventive peoples discovered soap making independently.

The legend says soap was first discovered by women washing clothes along the Tiber River at the bottom of Sapo Hill. The women noticed the clothes became cleaner with far less effort at that particular location. What was happening? The ashes and the grease of animals from the sacrificial fires of the temples situated on the top of Sapo Hill mixed with the rain, making soap which ran down the slope in the streams of rain water giving the women a wash day bonus.

You can see at a glance saponification, the chemical name for the soap making reaction, bears the name of that hill in Rome long ago, which caused one Roman washer women to comment to another, "My wash is cleaner than yours".

Page 15: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Organic compounds are those that are made mostly of carbon

Page 16: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Carbon chain molecules, with hydrogen filling up the extra bonding areas.

Can be one carbon, 2,3,….20… Non carbon parts are known as functional groups.

Page 17: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

What are esters? Esters are derived

from carboxylic acids. A carboxylic acid contains the -COOH group, and in an ester the hydrogen in this group is replaced by a hydrocarbon group of some kind

Page 18: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Lipids are a group of water INSOLUBLE compounds that include Fats Oils Waxes

Your cells are made of a lipid bi-layer.

Page 19: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

In a strong base or acid water , H-OH, willbreak apart the

R-COO-RInto

R-COOH and R-OH

Carboxylic Acid and Alcohol

Page 20: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Hydrolyzing fats in the presence of a base Like NaOH…sodium hydroxide.

Soaps are alkali metal salts (Na, K, or Li)of carboxylic “fatty” acids.When put into a NaCl mixture,

the soap separates from the glycerol

Page 21: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Review the work from your notebook from the past week.

Spend 5 minutes writing/reflecting about what you learned. Include specific examples.

Page 22: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Review the work from your notebook from the past week.

Spend 5 minutes writing/reflecting about what you learned.

Page 23: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Insoluble in water

~Apple wax C27H56

Broccoli C29

Tobacco C31

Page 24: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Low boiling points compared to similar weight molecules.

(only London/Van der Waal’s dispersion forces)

Page 25: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Branched alkanes have lower boiling points than straight.

More spherical molecules are more difficult to induce dispersion forces. (=weaker)

Pentane36

2-methyl butane 28 (isopentane)

2,2 dimethyl propane10

Page 26: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Petroleum-liquid mixture of

organic compounds: mostly alkanes and cycloalkanes.

From decayed animal and vegetable matter

Parts are separated by distillation

Natural Gas- Gas mixture of

methane (80%) and ethane (10%) and other alkanes

- Often found near deposits of petroleum

Page 27: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

2- butene

2-3 dimethyl butane

Page 28: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Cis = same side

Cis 1,2 dimethlycyclopentane

Trans = opposite side

Page 29: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Oxidation of an alkane, replace C-H bond(s)with C-O

bond(s)

Alkanes used as fuels

Alkane + O2 CO2 + H2O - ∆H

heat energy released

Page 30: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Substitution reactions

A halogen replaces a hydrogen

R-H + Cl-Cl R-Cl + H-Cl

Chloroethene

(Vinyl chloride)

Page 31: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Copyright © Houghton Mifflin Company. All rights reserved.

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Copyright © Houghton Mifflin Company. All rights reserved.

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Copyright © Houghton Mifflin Company. All rights reserved.

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Copyright © Houghton Mifflin Company. All rights reserved.

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Copyright © Houghton Mifflin Company. All rights reserved.

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Copyright © Houghton Mifflin Company. All rights reserved.

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Page 37: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Family of organic acids.Weak acids

Functional group COOH

or CO2H

Page 38: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Carbonyl C=O Hydroxyl -OH

A carboxylic acid derivative replaces the -OH (hydroxyl) group with another functional group.

Examples:• esters• acyl halides

Page 39: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Alkane = ethaneCarboxylic acid =

ethanoic acid

Replace the final e of the alkane with “–oic” add the word “acid”

Page 40: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Alkane = benzeneCarboxylic acid =Benzenoic acid(benzoic)

Page 41: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C
Page 42: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

The hydroxyl group -OH of the carboxylic acid is replaced by

-OR’

Page 43: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

R first-OR’ next. Change ”ic” to “ate”

Page 44: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Our favorite results so far:

Alcohol Carboxylic acid Name Odor

Page 45: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

C8H8O2 COOH (Ester)

Page 47: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

1) pi bonds ( π ) are broken

( π )1) sigma bonds ( σ )

formed to 2 new atoms

Page 48: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Hydrochlorination

Hydration

Bromination

Hydroxylation

Hydrogenation

Page 49: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Br2 to an alkeneCl2 to an alkeneIThe addition of a single halogen to each

carbon of the double bond.

The reaction is spontaneous, occurs at room temperatures, and needs no additional energy input.

electrophilic addition

Page 50: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Reaction of :1-hexene with bromine.

Cyclopentene with bromine.

Page 51: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

1) pi bonds ( π ) are broken

( π )1) sigma bonds ( σ )

formed to 2 new atoms

Page 52: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Hydrochlorination

Hydration

Bromination

Hydroxylation

Hydrogenation

Page 53: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Water H- OH adds to the double bond of an alkene.

An acid is required to act as a catalyst (H+)

ProblemAcid catalyzed hydration of

2-butene

Page 54: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Br2

H2O

H2

HBr

Problem:Hydration of 2-methyl-2-butene

Addition products of unsymmetric reagents to unsymmetric alkenes are called regioisomers.

REGIOSPECIFICREGIOSELECTIVE

Page 55: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Determines where an unsymmetrical reagent will react. Which regioisomer will be favored.

The electronegative part bonds to the carbon with the least number of hydrogens.

problems1-butene + HBrHydration of 1-chloro-2-butene (using an acid

catlalyst)

Page 56: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

3.8 (pg 85)3.9 (pg 85)3.10 (pg 86)3.11 (pg 88)

look up the following terms:electrophile , nucleophile, and

carbocation.

Page 57: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Electrophile: E+

electron poor reactant; seeks electrons

Nucleophile: Nu-

electron rich reactant; forms bonds by donating electrons. (to electrophiles)

Page 58: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

How many sigma bonds, and how many pi bonds are there?

Page 59: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

In a multistep process, bromine is added to all the pi electrons.

First mole of Br2 produces a trans product.

Second mole of Br2 produces a fully halogenated procudt.

Ethyne (Acetylene)+ Br2

Page 60: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

With a Ni or Pt catalyst

Alkynes are fully hydrogenated

C2H2 + H2

With palladium catalyst (Lindlar’s catalyst)

Only 1 mole of H2 is added and you end up with a cis alkene

Ni

Page 61: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

CH3CCH + H-Br

Follow Markovinkov for each step.

Page 62: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

3.40 a-f

3.42 a-e

3.53a

Page 63: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C
Page 64: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Alcohols ACETIC PROPIONOIC BENZOIC

SALICYLIC

Methyl

Ethyl

Propyl

Isoamyl

Octyl

Page 65: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Charcoal is used as a filtering material

The charcoal has a very large surface area per unit mass

1g has 500-1000m2 of reactive surface area

Page 66: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Has an affinity for organic compounds, gases, halogens.

Great to remove contaminants.

Charcoal filtration of Grape Juice.Sketch your lab set up, describe the

procedures, and results.

Page 67: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Molecules with empirical formula CH2O they are ‘hydrates’ of Carbon

Examples: glucose, fructose, dextrose Uses:

cell energy requirements cell structures

Page 68: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Monosaccharides (ex. Glucose) Simples carbohydrates Are the building blocks of other

carbohydrates Disaccharides

2 mono-sacs bonded together Polysaccharides

Large carbohydrates, polymers built of many monos

Page 69: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Aldehyde

Ketone

Aldose Ketose

Page 70: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Describe an isomer

Structrual = different bond pattern

Stereoisomers = same bond pattern

Page 71: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Two 3-d forms of a molecule with different orientations in space.

Stereoisomers are chiral. (Show handedness)

Try to superimpose your left and right hand.

Page 72: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Build chlro-bromo methanol. (use different color for the 2 halogens)

Determine if you have the R, or S version1. Locate the sterocenter.2. Assign priority based on molecular weight to each

attached atom.3. Orient the molecule so the lowest priority is

pointed away from you.4. Trace your finger in a circle beginning with the

highest priority to the lowest priority.5. IF the circle is clockwise, you have an R isomer. if the circle is counterclockwise you have an S

isomer.

Page 73: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

The mirror image of a chiral molecule cannot be superimposed on the molecule itself.

(an achiral molecule can be superimposed)

Build the following molecule(s).

2- butanol2-propanol

Page 74: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Stereocenter is a carbon with 4 unique attachements.

Build/Draw 2 chlorobutane 3 chloro cyclohexene

Identify the stereocenter in each molecule

Page 75: Salicyl alcohol acetyl salicylic acid. Saturated carbon chains C C-C C-C-C

Stereoisomers have identical chemical and physical properties.

Stereoisomers are OPTICALLY active. Our enzymes typically only react with 1

of the 2 stereoisomers. The binding sites for enzymes are based on a specific chirality.